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R3P/ICH2CH2I-Promoted Skeletal Editing of Cyclic Ethers via O/N Exchange
Yue Zhang1,2, Jin-Hong Lin1,2, Ji-Chang Xiao2
1Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China.
Organic Letters
|February 15, 2026
Summary
Researchers developed a new method for skeletal editing of cyclic ethers using O-to-N exchange. This process converts common cyclic ethers into valuable nitrogen-containing heterocycles, important in medicinal chemistry.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Functionalization of cyclic ethers is crucial in organic synthesis.
- Skeletal editing of cyclic ethers, particularly via O-to-N exchange, presents a significant synthetic challenge.
Purpose of the Study:
- To develop a novel method for the O-to-N exchange of cyclic ethers.
- To enable the direct conversion of readily available cyclic ethers into nitrogen-containing heterocycles.
Main Methods:
- A novel strategy employing a R3P/ICH2CH2I system was utilized.
- The method facilitates the direct conversion of cyclic ethers like tetrahydrofuran and 1,4-dioxane.
Main Results:
- The developed method successfully achieved O-to-N exchange in cyclic ethers.
- The transformation yielded nitrogen-containing heterocycles, prevalent in biologically active molecules.
- The reaction demonstrated broad compatibility with secondary and tertiary amines, providing products in moderate to good yields.
Conclusions:
- A new R3P/ICH2CH2I-promoted O-to-N exchange reaction for cyclic ethers has been established.
- This methodology offers a valuable route to synthesize nitrogen-containing heterocycles from common cyclic ethers.
- The approach is efficient and versatile for accessing medicinally relevant scaffolds.
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